1-Phenylethanol → HCID 66924294, compound

HRID 1364383Notes

Reaction equation

HRID 1364383 reaction equation
[H-].[Na+].[CH3:3][CH:4]([OH:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[F:12][C:13]1[CH:20]=[CH:19][CH:18]=[C:17](F)[C:14]=1[C:15]#[N:16].C(#N)C1C=CC=CC=1>CN(C=O)C.O>[F:12][C:13]1[CH:20]=[CH:19][CH:18]=[C:17]([O:11][CH:4]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH3:3])[C:14]=1[C:15]#[N:16]

Participants

7

Reactant 4

HCID 74091-PhenylethanolHCID 7505BenzonitrileHCID 24758Sodium hydride2×HCID 746952,6-Difluorobenzonitrile

Product 1

HCID 66924294HCID 66924294, compoundYield 86.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent3×

Procedure

Sodium hydride (60%; 316 mg; 7.9 mmol) was suspended in DMF and cooled to 0° C. sec-Phenethyl alcohol (966 mg; 7.9 mmol) was dissolved in DMF and added dropwise to the sodium hydride mixture. The solution was allowed to warm to room temperature and stirred for 1 hour. The solution was then cooled to 0° C. 2,6-Difluorobenzonitrile (1 g; 7.2 mmol) in DMF was cooled to 0° C. and the alcohol mixture was added dropwise to the benzonitrile solution and stirred for 2 hours. The solution was poured over 100 mL of cooled water. The solution was stored in the refrigerator for 3 hours and the solid was collected by filtration and dried under vacuum to yield 1.50 grams of 2-fluoro-6-(1-phenylethoxy)benzonitrile.

Workup

  1. temperatureThe solution was then cooled to 0° C
  2. stirringstirred for 2 hours
  3. waitThe solution was stored in the refrigerator for 3 hours
  4. filtrationthe solid was collected by filtration
  5. customdried under vacuum

Sources & evidence

ORD record
ord-434bede01c76461eb181ad9bfdca32c4
Source dataset
uspto-grants-2011_02
Patent number
US07888366B2

Reaction notes

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